Licensed Roofer Serving Winchendon, MA

"Hail punched through half our shingles last spring. Monterey Roofing & Maintenance handled the entire insurance claim — met the adjuster, filed the supplement, and we paid nothing out of pocket besides the deductible."

"Second roof Monterey Roofing & Maintenance has done for us. First one on our primary home, now our rental property. Same crew both times, same attention to detail. Drip edge, ice shield, everything by the book."

"The Golden Pledge warranty was a big factor in our decision. 25 years on workmanship plus 50 on materials. Monterey Roofing & Maintenance is one of the few local companies that can even offer it."

No Subcontractors

Every Winchendon roof is installed by our own trained crews, not subcontractors pulled from a labor pool. That means consistent quality, accountability, and a crew that knows our standards from the first nail to the last drip edge.

4.7/5 Stars | 338+ Reviews

Our reputation is built one roof at a time. 338+ homeowners across Monterey, Winchendon, and surrounding areas have rated us 4.7/5 stars. We earn every review. No incentives, no discounts for feedback.

17+ Years of Experience

We've been installing and repairing roofs for over 17 years. That experience shows in how we handle complex roof lines, unexpected deck damage, and insurance claim disputes. We've seen everything and know how to handle it.

GAF Master Elite Certified

Only 2% of roofing contractors in the country hold GAF Master Elite certification. That gives Winchendon homeowners access to the Golden Pledge warranty: 25 years on workmanship, 50 years on materials. It's the strongest warranty in the industry.